Bibliographical background about 1,5-bis(4-hydroxy-3-methoxyphenyl)-penta-1,4-dien-3-one compound and derivatives and its method for the preparation.
The compound denominated 1,5-bis(4-hydroxy-3-methoxyphenyl)-penta-1,4-dien-3-one is known since the year 1927 since E. Glaser and E. Tramer for the first time reported its synthesis with a 60% yield (Journal für praktische Chemie, 116, 331-346, 1927) from the vanillin and acetone in the presence of concentrated hydrochloric acid, used as a catalyzer.
Further, P. Ramanan and M. Rao synthesized this product in 1989 (Indian Journal Pharm. Sci., 51, 207, 1989) from 4-O-methoxymethylvanillin and acetone in an alkaline medium, obtaining a yield of 42% after purifying the same using the thin-layer chromatograph (silica gel).
In 1997, a group integrated by S. Sardjiman, et al. (Eur. Journal Med. Chem. 32, 625-630, 1997) developed a new variant synthesis using equimolecular quantities of vanillin and acetone in the presence of concentrated hydrochloric acid, reporting a raw yield of 89% (without purifying). For this reason, the melting point indicated in this procedure was 58° C. less than the one reported by Glaser and Tramer.
M. Artico et al. also obtained this substance one year later (Journal Med. Chem. 41, 3948-3960, 1998) only obtaining a poor yield of 18%. The melting temperature (114-116° C.) is lower than the one reported by Glaser and Tramer, what is makes think that the compound was not obtained pure in despite of the use of the chromatograph of column.
Additionally, we can find in the bibliographic revision the article of the American patent (U.S. Pat. No. 4,521,629 of Jun. 4, 1985) of N. Cortese et al. entitled: “Method for the preparation of 1,5-bis-aryl-1,4-pentadien-3-ones.” This invention reports to a method of preparing certain bis-arylpentadienones containing fluorine, that were used as intermediate compounds for the preparation of insecticidal substituted amidinohydrazones, but it does not protect the products that appear in our patent request.
Furthermore, the following documents of other patents related to this family of organic compounds were found:
1-“Hair tonics containing bis(hydroxyphenyl)pentadienones.” Authors of the patent: Morita, Kazuyoshi; Hamada, Kazuto. Company: Kanebo, Ltd, Japan. Country: Jpn. Kokai Tokyo Koho, 7 pp. Idiom: Japanese. CA-Number: 134:183278. PI: JP 2001048756, A2 20010220 JP 1999-224982 19990809.
2-“Skin-lightening cosmetics containing distyryl ketones.” Author: Morita, Kazuyoshi. Company: Kanebo, Ltd., Japan. Country: Jpn. Kokai Tokyo Koho, 7 pp. Idiom: Japanese. CA-Number: 131:149078. PI: JP 11209235 A2 19990803 JP 1998-10414 19980122.
3-“Acidic planting baths and methods for electrodepositing bright and ductile zinc-nickel allows and additive composition for these baths.” Company: McGean-Rohco, Inc., USA. Author: Canaris, Valerie M. Country: U.S., 8 pp. Idiom: English. CA-Number: 111:183131. PI: US 4832802 A 19890523 US 1988-206017 19880610 EP 346161 A1 19891213 EP 1989-305925 19890612.
4-“Photopolymerizable compositions.” Compound: Eastman Kodak Co., USA. Authors: Noonan, John M.; McConkey, Robert C.; Arcesi, J. A.; Rauner: Frederick J. Country: Brit., 19 pp. Idiom: English PI: GB 1425476 A 19760218 GB 1973-3986 19730322 US 3748133 A 19730724 US 1972-237929 19720324.
None of these four patents, either directly or indirectly, are related to the antiproliferate properties shown by 1,5-bits(4-hydroxy-3-methoxyphenyl)-penta-1,4-dien-3-one and its derivatives.
Taking into account the bibliographic revision performed by the company Bypropind Patents and Trademarks based on the tracking in the Chemical Abstracts collection, of Lifescience, of Biomed of Fiocruz library and by us in the Beilstein collection, we have concluded the there is no patent of that compound and its derivatives applicable in the cancer treatment or even the ultrasonic technique in despite of the compound has been synthesized in the year of 1927 and so that the patent request is possible and legitimate.